Legacy
by nightnovice
Summary: Story prompted by:  roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house. It is an AU story. Disclaimer: No profits being made here, just flights of fancy, please don't sue.
1. Chapter 1 - I am a Hayden

Story prompted by: roganjalex: Rory starts a relationship with Christopher parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

 **Chapter 1 – I am a Hayden**

Rory stood in front of the door, the door seemed ominous even though the home itself was no more daunting than that of her other grandparents. She took a calming breath and rang the bell, the maid answered and she informed her of her name and asked to see the Haydens.

"Lorelai Hayden, what a presumptuous girl you are and what makes you think you can claim the name or came to our home without invitation?" Francine asked after the maid had left the girl in the parlor.

"It is the name on my birth certificate, well one of them, I am formally named Lorelai Leigh Gilmore- Hayden, my father is your son after all. I thought it was time to meet you both and prove I am not a mistake. I use the Gilmore name because they are proud of me and my accomplishments. Is it wrong that I want you to be proud as well?" She handed them a portfolio of her awards, report cards, some pictures of her from birth to present and a certified copy of her birth certificate. She then went to the drink cart and poured herself a glass of water and sat across from the befuddled pair.

Straub and Francine perused the information and eyed the girl warily. She sat patiently and quietly observed the sitting room. There was a painting of her father and grandparents, much as at the one of her mother at the Gilmore's, some tasteful LaLique statues depicting a woman reading, a woman gathering flowers and a mother and child. A fresh vase of flowers some smaller nick knacks and a fire kit. The furniture was of good quality and had a hint of a texture rather than a pattern and the decorative pillows appeared to be replica of English tapestry. She sat upright, sipped her water and awaited the inquisition.

It was Straub who spoke first, "What do you seek to gain by coming here, showing us this information?"

"I wish to know you, you are my grandparents, I don't want to be hidden away as a shame or burden, I want you to be proud of me, get to know me and maybe in time I can call you grandma and grandpa." Rory tried to hide the nerves in her voice.

Francine looked at her, "You have your father's nose, did you know that and it appears you have the Hayden backbone as well."

"Thank you, I hope to have the best attributes of both my parents and grandparents." She smiled demurely.

Straub looked at her and snickered,"It's not money you are after? I know your father contributes little to none of that and the Gilmore's pay for that school."

"I am well cared for, true the Gilmore's pay for my school, but I work hard and get good grades and when we can my mother and I will repay them. I did not come for money, but if that is all you think of me, I guess I will take my leave. I had hoped to at least be friends." She stood trying to calm her breath and stood to leave. "I wish you all the best and I hope you have all you want in life."

Francine stood and hurried to her side,"Please don't go, I would like to get to know you, it's almost lunch time can I convince you to stay?"

"Yes, forgive my suspicion, stay, get to know us a little." Straub added.

Rory breathed a sigh of relief, "Yes, I will stay, and all I really want s to know you, I didn't plan my conception or birth and I really want to know more about you both, my family and maybe some stories from when my dad was a kid?"

"Of course dear, we would like that too. Now before we retire to lunch, do you have any allergies?" Francine inquired.

"No, I have no allergies that I know of." Rory replied returning to her previous perch on the settee.

"Good, I will let cook know you are joining us and have the table set for one more. If things go well would you be willing to visit with us more often?" Francine was hopeful.

"I would like that very much." She beamed at them and their hearts were warmed by her genuine cheer at their tentative acceptance of her.

They rose to enter the dining room when the maid informed them that lunch was served. She asked questions about the family and they filled her in on her history. This would be the beginning of more than she could have hoped, she enjoyed the simple meal of French onion soup and turkey sandwiches followed by an assortment of small cakes and coffee. When the meal was completed Rory gave them each a small hug setting an appointment for two weeks from this meeting to meet again.

Rory left the Hayden house happy and light and drove the 20 minutes to her home in Stars Hollow bubbling to tell her mom all about it.


	2. Chapter 2-Proud So Very Proud

Story prompted by: roganjalex: Rory starts a relationship with Christopher parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

A/N: Hi everyone, I want to thank those following, favoritism and reviewing! A lot of your questions will be answered in future chapters. Please stick with it, I think you will like it. Please also read and review my other stories, they are complete but I love feed back, encouragement and inspiration to keep writing. I appreciate you all so much!

 **Chapter 2 – Proud – So Very Proud**

Rory parked the jeep in the spot in front of the crap shack and happily walked to her home.

"Mom, are you here, I have great news!" She looked around the room and ventured into the kitchen and started the coffee pot.

She looked at the fridge and saw a note: Sorry sweets, late night at the Inn, Toby called in sick. There is money under the monkey lamp for dinner or drugs, just kidding, don't get Indian and if you do burn the house down. Love your beautiful Mother.

Rory laughed at her mother's antics and considered her Saturday night alone. She contemplated what to do and considered calling Lane to join her. As she was musing over her options her phone rang.

"You have to help me!" Paris began by way of greeting, "Madeline is dragging me to one of those parties and I don't want to go, you have to come so there is a modicum of sanity and someone sober I can talk to."

Rory laughed, she an Paris had a strange friendship, mostly they were academic rivals and rescue friends, you know the type, the friend you call to get you out of a bad date, the one you call to go to a party you dread or even get you out of said party.

"Paris, I would love to help, but mom is working late so I am stuck. You could come here though, we could study, have dinner and you would be able to ditch Madeline honestly." She countered.

"I have to go, it's Tristan's welcome home party, it is a huge event, I am surprised your grandparents didn't make you go." Paris sighed.

Rory considered this new information. "That will work, I can call my grandparents and ask to attend and leave a note for my mom. Then when we get there we say our hellos and sneak into the library to escape until it's time to go. How does that sound?"

"Perfect, it is a cocktail affair so I am sure you have something, don't wear blue though I already am and Maddie is in green, Louise in red, got it? I will be by to get you in two hours." Paris didn't even await the reply and disconnected the call.

Rory quickly dialed the Gilmore home, "Hi Grandma, how are you this evening?"

"Rory dear - how good of you to call, to what do I owe the pleasure?" Emily replied.

"Well, I just received a frantic call from Paris begging me to attend the Dugrey party welcoming home their son Tristan and I was wondering if I was invited?" She rocked on her ankles and hoped.

"Of course you were invited, didn't your mother tell you? She told me you were studying and could not attend. I am sure the Dugrey's would love your attendance." Emily was assuring. "Do we need to send a car, you can't possibly drive that jeep."

"No thank you grandma, Paris is coming to get me, I understand the dress is cocktail, will my black slip dress with a wrap be alright?" Rory inquired.

Emily glowed at being asked her advice and considered the dress in question. "Yes dear, that would be lovely, and be sure to wear the necklace and earrings we got you for your last birthday, the pearls will be a lovely touch. We will see you there." Emily said and then disconnected the call.

Rory retired to her room to get ready for the evening. The phone rang as she was exiting the shower.

"Rory, what are you up to, please tell me you didn't get Indian?" Lorelai began.

"Hello to you too Mom, and no I didn't get Indian, I am getting ready to go to a party with the grandparents, Paris called frantic and begged me to go." Rory hastily explained.

"HA! I tried to get you out and like the mob they pull you back in. Well try to have fun and if you need to spend the night at your grandparents, that way I don't worry about you home alone." Lorelai mocked.

"That sounds like a plan I will pack an overnight bag. Oh and just so you know I had lunch with the Hayden's this afternoon and they agreed we should get to know one another, isn't that great?!"

"That is a discussion for another day, with lots of coffee. OK kid, I got to go, be good and I love you." Lorelai ended the call and gently banged her head on the reception desk. "Dammit kid, what are you doing to me?"

Rory finished getting ready and was just applying her gloss when she heard the car rolling to a stop. She grabbed her travel bag, phone, charger and wrap and headed to the door. She opened the door to a startled Paris.

"God Gilmore, give me a heart attack why don't you? Haven't you heard the person is supposed to knock before you fling the door open like that. Geeze!" Paris ranted.

"Come on Paris, I heard the car and figured you would be in a hurry. Let's go." She shut the door behind her and heard the lock click.

"What's with the bag? I don't recall this being a slumber party." Paris queried as the driver took the bag and placed it in the trunk.

"Mom told me to spend the night at the Gilmore's she won't be home tonight and didn't want me to be alone. I will just have it moved to their car when we get to the party." Rory explained.

"Lucky you, if my parents leave, I am alone ever since they decided I didn't need Nanny anymore. I miss her, but she opened a papusa shop and I can visit sometimes." Paris slid into the car and Rory slipped in beside her nodding to Madeline and Louise.

The drive to the Dugrey's was uneventful and the girls mostly chatted about the upcoming school dance and the dreaded Biology exam. They arrived and Rory directed the driver to her grandparents car to store her bag then followed the girls into the party. She immediately sought out her grandparents to inform them of the plan. She knew they would be more than pleased but it was important that they know so she was not left behind.

The girls made their way through the party, finding the hosts and the guest of honor speaking with the Hayden's.

"Rory, we didn't know you would be here, this is Michael and Amanda Dugrey and surely you know their son Tristan." Francine enthused and Emily who was just approaching stalled at the introduction. "Michael Amanda, this is Rory, our granddaughter, she is Christopher's girl."

Tristan looked at Rory with a slight awe, "Rory, nice to see you again."

"Hello Tristan, Michael, Amanda, thank you for having me. Welcome home Tristan, Chilton hasn't been the same without you." Rory replied and knew Monday would bring a bevy of gossip with this new information.

"My aren't you a lovely girl, we haven't met you before were you abroad?" Amanda queried.

"No, I just live in a small town and only began attending these events since I started at Chilton." Rory evaded and both Emily and Francine were proud of her diplomacy.

"Rory darling - there you are, I see you have met the Dugreys and Francine, how have you been?" Emily approached the group when conversation stalled.

"Hello Emily, so good of you to come it has been such a lovely turn out for our Tristan. Is your granddaughter here as well? " Amanda inquired.

"Hello Amanda, Michael, Tristan yes she is, Rory is my granddaughter as well." Emily observed their acceptance of this information and knew they had just put the story together. This was the child of the Gilmore / Hayden scandal.

"Well Rory aren't you fortunate that your grandparents are so well accepted in society. You are a lucky girl indeed. Tristan, why don't you take Rory here and show her the library, I hear she is quite the prolific reader and you write for the Franklin as well correct?" Amanda placed Rory's hand on Tristan's offered arm.

"Yes I do and thank you I would love to see the library." She and Tristan left the adults to talk and the other girls followed.

The adults watched as the group disappeared into the library, "Emily, Francine, she is a beauty, and smart too. You have done well with her. I am not surprised though you both are so impeccable." Amanda acknowledged.

"Thank you, we are very proud of her." Both women replied as if rehearsed and then looked at each other and giggled.

The group of youths entered the library, "Hayden, are you kidding me?! Why would you keep that a secret? You are the granddaughter of legendary Judge Hayden, wow, no wonder you are so good at debates." Paris was incredulous.

"Why is this such a big deal? The Gilmore's are known to be as well set and known as the Hayden's, why does it matter?" Rory was flabbergasted at the tone of accusation.

Tristan took the lead, "My family and the Hayden family own the largest law firms on the Eastern seaboard, you are now inline to be the Hayden heiress and that will make you perfect for me in their eyes."

Louise giggled, "I bet they are signing a prenup as we speak, you are in deep girlie. Here we thought you were some churchmouse from Hicksville and you have a better pedigree than we imagined."

Madeline piped up, "The only other suitable match would be Huntzberger, but I don't see that happening."

Rory looked at the group as if they had grown a new head. "Huntzberger as in the media mogul? You are all bent, I don't think my mom would allow any of it. She has kept me out of so much already."

"Nope, no more girl, you are out and trust me, every trust funder who is able will be around to land you. You are the great hope." Paris supplied. "My friendship with you will gain some parental approval as it will for Maddie and Louise."

Tristan playfully leered at her, "It looks like I am candidate number one now though, so how about it Mary, up for dating the soon to be Law king?"

Rory laughed at that, "Maybe, we'll see." She snuggled up to him and he was dumbfounded. "Enough about me and my future hubby, show me the library."

The teens laughed and spent the remainder of the evening hiding out in the library. It was there Emily found them and several other youths who had joined them in a rousing game of pictionary, she stood back and enjoyed their antics until Rory noticed her.

"Grandma hi, is it time to go already?" Rory embraced her grandmother cordially. The group stilled and looked to the door for other parents to arrive.

"I hate to take you from your friends, but it is quite late, ready to go?" Emily smoothed her hair behind her ear.

"Sure grandma, I will just say goodbye and meet you at the door." She excused herself then went to say goodbye and retrieve her wrap.

Tristan followed her as she exited the door,"Rory, just a minute, do you want a ride home tomorrow?"

"That is really sweet, I would like that." You know the address I guess I will see you at one after brunch, or better yet I am sure my grandparents will insist. If you want you can come, we usually start at 11:30 if you want to stop by, I am sure they won't mind."

"Thank you, I will do that." Tristan kissed her cheek and then returned to the library.

Rory found her grandparents, said goodbye to the hosts and waved to the Hayden's as the exited.

Once they were in the car Emily asked "Rory, what happened with the Hayden's? They were so different towards you than they have ever been. I mean even last Friday they were hardly civil."

"Actually, after everything that happened I decided to put the record straight, meet them face to face and show them the real me. Then I had lunch with them today and we kind of started to get to know one another. I hope that's OK?" Rory was nervous for the second time today.

"That's fine Rory, was it your idea or theirs?" Richard asked.

"Well grandpa, after last week I wanted to let them know that I wasn't anything to be worried about, that I was a good student, a good citizen and not anything like they thought." Rory explained, "We are having lunch again in two weeks so I can learn about more of their family."

Emily was concerned but tried to be encouraging, "Well that sounds like you did the right thing, Francine was simply glowing going on and on about you today. It was quite a surprise. She simply went on and on, you would think she had a dossier or something, she was on about your grades, awards and acting as if she had known you for years."

"Well grandma, I kind of put together something of a book on me, it had pictures, report cards and such, I wanted to prove to them that I am not an accident or a disgrace." Rory's voice was a little embarrassed.

"They were wrong, and you never should have felt the need to impress them, but I am glad you took it like a Gilmore and proved them wrong." Richard had pride in his voice.

"Oh, grandma, Grandpa, Tristan offered to drive me home tomorrow so I invited him to brunch, is that OK?" Rory rushed.

"That is fine dear, just fine." Emily beamed at Richard and he smiled.

They arrived at the house, the driver handed the maid Rory's bag and the family retired for the evening.


	3. Chapter 3 - Not So Lazy Sunday

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

A/N: Hello again, I am so glad so many of you are reading, favoriting and commenting, I corrected the 's above although I didn't understand what the original comment meant, I figured it out,this chapter, helpful if you note a typo location, it will be fixed quicker. Remember this is AU, which means, I created the timeline and tweaked the characters to fit this story, if you read my other stories you will get it, feel free to comment on those as well, feedback is always interesting and with the story it is a bit different than any I have read and I hope you all enjoy it!

 **Chapter 3 – Not so Lazy Sunday**

Tristan arrived at the Gilmore home and was promptly lead to the dining room and seated beside Rory.

"Sorry if I'm late, I hope I didn't hold anything up." Tristan said as he took his seat.

"Nonsense my boy, we were expecting you and just sat down for coffee." Richard assured.

"Tristan, how was your time abroad?" Emily asked and Tristan tried not to choke on his juice.

"Actually Emily, I wasn't abroad, if I am going to be spending time with Rory, it is best you know the truth. I got into a bit of trouble last year and my parents sent me to North Carolina to military school. I can assure you I learned my lesson and will steer clear of disruptive elements." He reported.

"Honesty is an admirable trait young man, I am sure you will go far in this world." Richard said as he dug into his grapefruit.

Breakfast went well and soon Tristan was loading Rory's bag into the trunk of his mustang convertible. The two youths took the road and after a while Rory noticed they weren't headed towards Stars Hollow.

"Tristan, where are we going? You said you were taking me home." Rory asked turning slightly to see him more clearly.

"Well, I figured since I had you hostage for a while I would take you to the Glass House, you haven't seen it have you?" He had a sly grin.

"No, but my mom is expecting me at 3 and it is 1:30 so I will have to call her so she knows I am safe." She flipped her phone and left a message on her mother's voicemail, grateful that she didn't reach the woman herself and endure the mocking.

The teens parked and Rory noted the lack of visitors."Uh, Tristan, I think it is closed."

"Not to us, my parents are major contributors and I called ahead for a private tour for us. Is that OK?" Tristan looked nervous.

"Wow, thank you, I think it is really nice of you to think of it. What can you tell me about it?" She looked at him and he took her hand and lead her to the waiting docent.

They enjoyed the tour and he took her home and was surprised as he pulled up to her home that it was so simple. He noted it was small but well cared for and not at all what he expected for a girl from such a prestigious pair of families could live so humbly.

Rory noted his stare and felt a little ashamed. "I know it's not grand or anything like your place, but it's home." She let him follow her up the stairs and she opened the door. "It looks like mom isn't home yet would you like to come in? I can make coffee."

"Yeah that would be nice. He handed her the bag and she tossed it in her room and went to make the coffee. He took advantage of her absence and walked around the small living room admiring the cozy decorations and warmth it held as opposed to the cold and formal home he was brought up in. There were pictures of Rory in several festive costumes and with a Korean girl and several with her mom. He was holding a picture of her as a baby when she walked in holding two cups of coffee on a tray with some Twinkies, cream and sugar.

"Sorry, my mom is a little picture happy." She set the coffee tray on the table and picked up a cup taking a long sip and making this mewing noise.

Tristan stood still looking at her and in odd admiration of her passion for the beverage.

"I really needed that, my grandparents don't approve of the habit so I refrain when I am with them." She sighed contentedly and plopped on to the couch patting it for him to join her. "So tell me about military school, was it hard, were you lonely?"

Tristan was touched by her inquiry, "It was military school, they were degrading, cruel and as for being lonely there was no time. Every single minute was scheduled and after my time was up, I found myself missing the structure. I still get up at 5 and go for a three mile run. I think it was good though, I learned to be in control of my surroundings and aware of the consequences of my actions."

"Wow, that sounds kind of horrible and so 1984, I am glad you are back. I really appreciate you taking me to The Glass House, it was beautiful, but I can see why it closes in the winter, it must not be very warm. I really would love to see it under the stars that must really be something." She offered him another Twinkie and he accepted happily.

"You are odd, I am glad we spent today together. You are nothing like I expected." He bit into the Twinkie then took a sip of the coffee. "You make excellent coffee."

"Thank you, it's not as good as Luke's but I am working on it. What do you mean I am not what you expected?" She looked at him expectantly.

"Well your grandmother Hayden spent the night talking you up to all the ladies of the DAR I don't think that anyone knew it was you until you arrived at my party. Heck I was half expecting some bookish wallflower with thick glasses and a bulb-nose to be introduced. You didn't hear this from me, but Francine Hayden was speaking to my mother about me being your escort on your coming out party. Finding out it was you was the highlight of my night." He was happy to explain as he indulged in another Twinkie.

"I had a debut, how is that different?" She got up leaving him time to think and retrieved the coffee pot to refill their cups, then returned the pot to the kitchen and brought out bottles of water.

"You are the consummate hostess, thank you. When you debut, you are presented as marriageable, a coming out announces your importance in society. It is kind of a big deal, not all girls have a coming out, just truly, for a lack of a better word, valuable girls, girls with excellent breeding, background and potential. It is arcane I know, but as far as Hartford goes, you being formally presented, it is a big deal It's why I was asked to be your escort, they want you to look like you belong. I'm sorry Rory, I know it isn't you, but you will have to do it now that Francine has made such a deal." He held her hands in his, consolingly.

Lorelai walked in to her home finding Rory and some boy sitting on her sofa sitting comfortably, intimately even, she was surprised but decided to go with it.

"Rory, I'm home, hope the bikers and band have gone, ready to gorge on Chinese and a movie night? Hello boy I have never met who is holding my daughter's hands way to intimately. The first words I should hear from your mouth are Hello Lorelai I am 'insert your name here' and I have no interest in defiling your precious daughter." She looked him expectantly.

Tristan rose and stood at attention, "Hello Lorelai, I am Tristan Dugrey of the Hartford Dugrey's owners of the second largest law firm on the Eastern seaboard. I attend Chilton with Rory, have just returned from military school and have no intention of doing anything to your daughter against her wishes."

Lorelai considered his response and laughed, "This is ET, the Son of Satan, the boy who dubbed you Mary, in an odd way laying claim to you so all the other boys were afraid to even come near you? You are holding out on mommy, he looks like he just walked off a Tommy Hilfiger ad."

Rory looked at her mother with appall, "Mom, Tristan is here as my guest, he took me to see the glass house, we have pictures."

"Oooh, the Glass House, that must have been something, but hey isn't is closed for the season?" She looked at the boy to confirm her suspicion.

"My parents are major contributors, it is never closed to us, I can arrange a tour for you if you so desire." He was calm at her accusation.

"You bet your sweet bippy I will take you up on that, new boy with a defilers heart, what are you up to this fine night? Tomorrow is a school day after all." Her tone spoke volumes.

"Actually, Rory has raved about Luke's Diner and I hoped that we could dine there before I returned home. I also understand the owner is quite fond of you both so his approval is imperative." Tristan simply stated.

This actually stalled Lorelai's barbs, he was willingly facing Luke, he understood the significance and after Dean breaking her heart at a town event, maybe this boy wasn't so terrible.

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P.S. if you want to know more about the Glass House:it is Glass house dot ORG


	4. Chapter 4 - The Inquisition

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

 **Chapter 4 -** **The Inquisition**

Tristan opened the door to the quaint diner and allowed the ladies to enter first and continued to hold the door while a few patrons exited. He then sat at the table with them and glanced at the menu.

"So tell me daughter of mine, why was ET holding your hands so inappropriately when I came home and how much further would it have gone had I not arrived?" Lorelai had a mischievous glint in her eyes as she stared at her daughter forcing her to blush.

"Actually he was comforting me, I just heard I have to have a coming out party now that the Hayden's have accepted me. Really mom we have only just started this friendship, I don't know why you have to make every male / female friendship into something untoward." Rory sighed and gave Tristan an apologetic smile.

The conversation stalled when Luke came to the table, "OK, I know what you two want, but what about you?" He indicated his pen to Tristan.

"Tristan Dugrey sir, I have heard nothing but praises of your fine establishment and would happily have what they are having." He smiled his charming smile.

Luke quirked a brow, "It's your funeral, Cesar three Gilmore plates." He walked away and returned with three cups and a pot of coffee and proceeded to pour for them then returned to the counter to start another pot.

Tristan was awed at the sound both women made while they sipped on the precious brew. He lifted the cup to his lips and understood their sentiment, this was by far the best coffee he had enjoyed and he had been to Columbia. Luke soon returned to their table with three large plates topped with burgers, fries, and a platter of chili cheese fries, Tristan couldn't help but reveal his shock at the sheer quantity of it all. The burger did smell heavenly though and the fries were a perfect golden hue. Luke snickered at his face and whispered 'Rookie' as he left them in his wake.

"What did you expect a couple of salads with delicate strips of grilled chicken. Psha that is not how a Gilmore Girl eats." Lorelai scoffed and took a bite of her burger.

"How often do you eat like this?" Tristan said as he chomped on a fry, they were as good as they looked.

"Pretty much always, you should be around for a movie night sometime we get a bunch of Chinese, pizza, tater tots, popcorn, candy and ice cream." Rory was enjoying some chili fries as she explained. "We are a medical marvel, it is probably our coffee consumption tied combined with our rapid style of banter that burns up so many calories."

"At school you barely have a sandwich and chips, you must be starving most of the day." Tristan was marveling at how quickly their meals disappeared.

"Not really, I find it easier to study if I am a little hungry it keeps me focused." Rory explained, "So mom, pie or do you want to get Ice cream next door?"

Lorelai pretended to ponder, "Pie and ice cream right here, Luke made apple pie today and I love it hot and gooey with the ice cream melting over it."

Tristan was surprised to see he had cleared most of his plate, but the thought of dessert did not appeal in the least. "Does Emily know you eat like this? How did this happen? I am stuffed and you guys are having pie?"

"Emily would be appalled, as would Francine and the rest of Hartford. We eat as society dictates when in their presence so as not to upset their delicate sensibilities but when left to our own device we more than make up for it. Mom left Hartford and decided we could eat whatever and as much as we wanted." Rory explained as Luke approached with the pie without prompting.

"How did you know they wanted pie, they never even ordered?" Tristan looked at his plate and tried to figure out where he would put any of it.

"They always have warm apple pie with ice cream on Sunday's, it's what they do. So what's your deal, you gonna be coming around here more often?" Luke stared at him in a way that made Tristan consider his answer carefully.

"Well, I hope so. I just returned from military school and have been asked to be Rory's escort for some upcoming events. I am hoping to be around a lot more." He hoped his answer was satisfactory.

"Know this, this girl is special around here and we are all watching, hurt her, we hurt you. Got it?" Luke had his arms crossed over his chest.

"Yes sir, and you don't have to worry about how I treat her between society and this town I am being very carefully watched in my treatment of her." He looked at her hopefully.

Tristan followed Luke to the counter, "I'll pay their check sir." He had his wallet in his hand. Luke handed him the check and he was surprised with how reasonable it was. He tipped generously and returned to the ladies who were done with their own pie and had begun to make short work of his.

"Well, all paid up, I am ready when you are." He smiled at them.

"Thank you, you didn't have to do that." Rory smiled at him,"Would you like a tour of the town before you head back?"

"My pleasure, and a tour sounds great." He replied.

"Well, I have seen the town so I think I will sit at the counter and bug Luke for more coffee. You two have fun and remember everybody's watching." She smiled evilly and turned towards the counter.

The teens exited the diner and Rory took his offered arm as she led him through the small hamlet. She showed him all the sights and as they were approaching the Inn she seemed pensive.

"What's wrong, did I do something?" Tristan looked at her feeling a bit worried.

"No, not at all, I was just deciding if I should show you or not, but I think I can trust you." She took his hand and led him to a small shed behind the Inn. She opened the door and turned on the light revealing rose printed wallpaper and a comfy chair and a small tub with a toilet. "This was our home until I was ten, my mom put up a curtain to divide it and in the summers we would watch the events at the Inn from the lawn here. My mom started as a maid and Mia, she owns the Inn, would watch me."

Tristan was overwhelmed and without thinking he pulled her to him and kissed her, "You are amazing, you come from two of the most elite families in Hartford and you were raised here. Your mom is very brave and she has raised an amazing woman."

Rory looked at him and pulled him in for another kiss, "I guess this makes us more than friends, but what exactly?"

Tristan stepped back and held both of her hands to his chest, "I would like you to be my girlfriend, it's all I ever wanted since the first time I laid eyes on you Mary."

She smiled at him, I would like that, but can you make sure no one calls me Mary but you? I want to keep it special."

"Believe me, once the school knows we are dating no one is going to think you are a Mary anymore." He leered playfully and pulled her in for a kiss. "I should get you home it's getting late and it is a school night." They kissed again and he wrapped his arm around her shoulder and they walked to her home quietly discussing their plans for the next day and the week ahead.

Lorelai watched the pair as they approached, "Lucy, do you have somesing to tell me?"

"Mom, Tristan has asked me to be his girlfriend and I have accepted. That means you will definitely be seeing more of him around here." She beamed at him.

Lorelai held her tongue, "Welcome to the fold Tristan, be on your best behavior."

"I will be, and I will see you in the morning when I come to get Rory for school, should I stop by Luke's for coffee first?" He looked at both women who were looking at him as if he sprung a new head.

"You don't have to pick me up for school, I can take the bus, it is too far out of your way." Rory explained.

"But Rory coffee delivery?!" Lorelai whined.

"I insist, I won't have my girlfriend on a bus, it's either I pick you up, send a driver or buy you a car." He tapped his foot and Lorelai looked amazed.

"Do you treat all your girlfriends this way?" Lorelai queried.

"Nope, they all had cars and Rory is special, besides once the announcement of her relationship to the Hayden's goes to press it will be much safer for her." He explained and felt a bit of pride in the anticipated win.

Rory looked at her mother who was acting like a begging puppy, " Okay you both win, just don't forget the coffee mister." She leaned in and kissed him sweetly and he strode to his car victorious.


	5. Chapter 5 - What Monday Wrought

Story prompted by: roganjalex: Rory starts a relationship with Christopher parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

A/N: Thanks so very much to all who have reviewed and been so encouraging! I also thank all who favorite and follow you rock!

 **Chapter 5 – What Monday Wrought**

True to his word Tristan arrived at the Gilmore house with coffee and a bag that contained 2 donuts as well as a muffin, Rory grabbed a coffee and the muffin handing Lorelai the donuts and second cup. Tristan grabbed her backpack and put it in the trunk then opened the door for her to enter. The drive to school was quick and Tristan pulled into his assigned parking space, he went around and opened her door then retrieved her backpack and together they entered the school. They soon arrived at her locker and he set her bag down then pushed her up against the locker and kissed her for all she was worth. Rory was surprised at first but quickly reciprocated his efforts.

"Do you mind Tristan, barely back one day and already spreading the love. Rory isn't going to appreciate you impregnating someone against her locker. Hey are you even listening to me?" Paris slapped his shoulder causing him to pull away from a dazed Rory and Paris gasped. "Rory are you kidding me, this walking STD and you are kissing?"

"Paris, calm down, he is my boyfriend, he is allowed to kiss me." She turned and attempted to open her locker. Tristan tapped it and it popped right open, she beamed at him then proceeded to transfer contents from her bag to it and retrieve the books needed for her first class.

"Rory, I need to check in with the headmaster, I will see you after your first class." He leaned in and kissed her sweetly, "Bye Paris, don't forget to breathe."

"Rory Gilmore-Hayden! What are you thinking dating Dugrey, are you drinking the purple Koolaid, buying into the dynastic plan? We weren't kidding this will make Hartford a buzz with speculation." Paris ranted waving her arms. Louise and Madeline just looked on in amusement.

"Gee Paris, take an ad out already. It's just Tristan, and we are only 16 and 17, there is no dynastic plan." Rory stated rolling her eyes at her overstressed friend.

"Don't roll your eyes at me missy, you'll see by lunch the whole school will be thinking of you as Mrs. Dugrey." Paris huffed and went to find her locker Madeline and Louise at her heels. The first bell rang and Rory went to find her class.

The day went quickly and Rory was only a little harassed until she found herself in the lunch line.

"There she is, the Hayden chick dating Tristan, what's so special about her. Isn't she the creepy one who sits alone reading and listening to her walkman?" A girl behind her stage whispered to two others.

"You know he'll dump her by the winter formal, he likes excitement and she is so dull. She doesn't even have a car or the school socks."

Rory tried to ignore them but their obvious distaste for her made her stomach turn. She paid for her tray and went in search of a table. She was so lost in thought that she didn't notice Tristan steering her to his table. He took her tray and set it by his.

"Hey, earth to Rory, are you in there?" He waved his hand in front of her eyes.

"OH, hey Tristan, sorry I was just in my own thoughts." She sat down in front of her tray and began to look for her book and walkman from her bag.

He reached over and foiled her pursuit. "Nope, not today, I wanted to introduce you to some people." He proceeded around the table, "These three miscreants just transferred in from Zugberg they are Seniors but it is good to know them, Logan Huntzberger, Colin McCrea, Finn Morgan and Robert Grimaldi, the ladies you know except Stephanie Vanderbilt. They are good people to know and no one can orchestrate a sub-party faster than them."

Hello's all around then Logan spoke up, "So Ace tell me, how do you like the Franklin?"

"It's not the Times or Journal, but it will do. Do you write Logan?" She took a sip of her soda and waited his answer.

"Well of course, can't sign on to a paper and not write, but I like to edit too, it's half the fun Ace" He chuckled lightly and was shoulder nudged by Colin who was attempting to warn Logan's flirtations off. "So tell me Ace, why haven't I seen you at any of the parties, I attend the Gilmore Christmas soiree every year since I was five and I don't recall ever meeting you, and with those blue eyes I think I would remember."

"I don't live in Hartford, although my boyfriend Tristan here assures my days of hiding out are numbered." Rory reached for Tristan's hand and he held hers happily. "Why do you keep calling me Ace?"

"You are an Ace reporter, I read a few of your articles and especially liked the parking lot one, never knew there was interesting information on concrete." He winked and Colin sighed.

"That's my Mary, she can take any old story and craft it with style." Tristan kissed her temple and she smiled demurely.

"So tell me girlie, how long have you and Tristan been doing the mattress mambo?" Stephanie teased.

Rory blushed furiously, "Uh, we only started dating yesterday, it's still all new."

Stephanie beamed, "Now I get the Mary thing, totes cute."

Rory finished her lunch and got up to leave the table, "Well it was nice meeting you all, see you around campus." She began to shuffle her bag onto her shoulder but Tristan took it from her then placed his hand on the small of her back and waved goodbye while escorting her out.

The pair exited the dining hall and she tried to excuse herself to the library, "Hey, what's wrong, why are you trying to flee, did I do something?" He held her hand preventing her exit.

"No, I am just not used to the attention and Logan made me feel like I was under a microscope. It felt icky, then Stephanie asked about … well you know and then – Mary, why would you want to be with a girl like me? I have only had one boyfriend before and that was, as Paris puts it - Puritan, we never..." She blushed and dipped her head, I mean I am not a prude, and so you know I am on birth control, but it didn't seem right." He led her to an empty classroom and they sat down. "I know you are experienced, heck most everyone here is, I just, well, my mom was only 16 when I was born, she wants me to live the life she never had, so I worry about – well everything."

Tristan considered all she had said and a light went off in his head, she wasn't only a virgin, she was trying to keep herself from the path that led her mom to being a single mother and missing so much of her life. He pulled her from her chair and into his lap.

"Mary, it's okay to be scared, worried and uncertain, I am too if that helps. Look I have had sex, but it wouldn't be just sex with you, I am not in a hurry to do anything you aren't comfortable doing. We will take this one day at a time and if and when you are ready, I will be too, I mean I hope it will be me." He noted her deep crimson at this declaration. "I want you to be comfortable and happy with us, really, I want a real relationship, sex isn't all there is, there has to be a foundation. While I was away I had a lot of time to think about what I did to deserve being where I was and one thing I realized was that I took advantage of everything and everyone, that is why we couldn't be together the first time. I was an arrogant jerk, you deserve a gentleman, and I promise to be one. I mean it Mary, I want this to work and I won't push you ever." He kissed her temple and pulled her to his chest. "Hey, isn't your birthday in just a few weeks, you'll be 17, any big plans, wishes?"

"You think we'll make it to my birthday? The girls in the lunch line gave us 'til Friday tops. They said I was mousy and weird and a loner." She hung her head against his chest.

He lifted her chin and kissed her soundly, "Mary, don't listen to them, you are beautiful, smart and so much better than them and as for the loner thing, you will be at my table and trust me now that the three and Stephanie have you in their sights you are never going to be alone. It'll all be okay soon baby, just don't let the gossips get to you." He hated how insecure she was, her mom had done a number on her, didn't she know how beautiful she was. " You are beautiful, you know that right?"

"You think so?" She looked at him with her eyes wide.

Just then Logan and company entered the room, "Hey Ace, we found you, why did you leave we were just getting to know you." He took note of her careful position on Tristan's lap, she looked small and afraid like a wounded kitten. "I hope we didn't make you uncomfortable, we can be a little ruff around the edges but we mean well. Say what are you up to Saturday we can all go to the mall for some shopping therapy and a movie." He sat across from the pair straddling the chair.

"Ooh, shopping, we can for to Forever 21 and get some fun clothes then go clubbing!" Stephanie enthused catching Logan's cues.

"Luv, we can teach you all about the pitfalls of this life we are thrown into so you survive without so much as a bruise." Finn tossed in and Tristan gave a thankful smile to his friends.

Rory looked at the group that now surrounded her, this was her new reality, the society her mother fled was now her responsibility. " That sounds nice, we can have breakfast in my town at Luke's you will all love it then we can do the mall and a few clubs, I should arrange to stay at my grandparents if we are out late in Hartford."

Stephanie laughed, "Sweetie, if we go clubbing, its New York and you and me can be roomies at the Ritz or hey, I think the Hayden's have a loft, we can ask them to stay there."

Rory considered this bit of news, "I don't think my mom would let me go clubbing in New York."

Tristan intervened, "You are right, we'll save New York for another outing, you spoke about an art movie house in your town, we can do that."

Rory lit up, "That would be amazing, you could get rooms at the Inn and we could have a great time in my town!"

Colin looked to the others and spoke up, "Yeah doll, that sounds swell, we can meet up, have breakfast, go shopping then wrap up with a classic film at your local theater." He tried to keep the sarcasm from his voice, it all sounded so TV movie of the week, a real life after school special. He saw what his friends did though she was a newbie, a lost lamb in a sea of wolves. They had to help her toughen up even if it meant they slowed down for a bit.


	6. Chapter 6 - The Wind in the Willows

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house.

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

A/N: Quick point of clarification, this takes place during Rory's junior and senior years, Dean broke up with her at the marathon and Tristan is returned from military school as many of us wished. Logan, Finn, Colin and Stephanie are Seniors headed to Yale. Rory is not as much as she is in the show, she likes society and she and her mom are a bit at odds because of it. Logan flirts with Rory because he likes her and he is a player, he flirts. The basic time frame follows the original series and is the late 90's early 2000's. (As a side note, my characters only look like the ones on the show they mostly follow a niece and her friends who was in her teens and an East Coast socialite when the show was on.)

 **Chapter 6 – The Wind in the Willows**

The SUV pulled into the sleepy hamlet stopping across from building labeled both 'William's Hardware' and 'Luke's' the youths piled out and made their way to the diner where Rory and Tristan were already seated. The group stood out as the socialites they were sharply dressed in designer clothes they earned stares from the townspeople. Logan sat across from Rory and Stephanie sat to her right while Tristan was on the left, Colin and Finn took the remaining seats.

"So this is Stars Hollow, population 3325 according to the welcome sign and boy don't we feel welcome." Colin snarked in a mock country drawl as he sat.

"Don't be a jerk Colin, I think it's cute and look they even have a real gazebo." Stephanie giggled gleefully. "I bet it was great growing up here, you probably know everyone and they all know you. I bet we can ask anyone here and they would have a Rory story to share."

Luke came and distributed menus then refilled Rory's coffee as Tristan placed his hand over his and requested water. He asked what drinks were wanted then left them to decide while he gathered more coffee and waters.

They all ordered what Rory was having except Tristan who ordered the chilaquiles. Luke snickered realizing Tristan had wised up and his friends were about to learn a big lesson. Realizing how much food was about to be delivered Rory pulled over a two top to extend the table and was grateful the breakfast rush was over and lunch a while away. The group was puzzled and Tristan just grinned. Luke and Cesar returned with the plates of 2 large chocolate chip pancakes, 2 eggs, 2 bacon,2 sausage, Jess was just behind them refilling any takers on the coffee.

Logan's eyes went wide with the sheer size of the meal, "Ace you are going to eat all of that, how can you eat that and not be 400 lbs?!"

Rory smiled as she topped her pancake with the whipped cream Jess brought over and offered it around, the only one who accepted was Finn. "My mom and I eat like this all the time, it's probably the coffee and fast banter that keep us so thin, but whatever it is we are happy for it."

Tristan laughed, "It's a rookie mistake ordering what Mary orders, I did it my first time and I swear I was full for two days. They also have this crazy sugar fest for movie nights, you wind up in a coma and hungover the next day from it."

"What good is a hangover without the booze?" Finn lamented as he enjoyed the over the top breakfast.

They watched in awe as she finished her breakfast and half of Stephanie's all while consuming more coffee than they could imagine.

"Ace, I got to hand it to you, I think you are a medical marvel, you should be studied. I'll get the check, the entertainment was that good." He rose to go to the cash register and felt the tightness in his overfull belly, she was a wonder. While he waited he lamented having not met her first, she was a beauty and could keep up with him, but she was Tristan's girl and until that ended he would have to bide his time.

The group waited outside and Rory took Steph to see the gazebo up close giving the boys a chance to gossip.

"Tristan, are you serious, that girl can eat, don't you worry she'll get fat or maybe she is bulimic." Colin cautioned, "No one needs to date a nut case who binges and purges."

Tristan looked at his friends and was disappointed, "You guys saw, she loves food and coffee, she wouldn't eat just to throw up I have been with her long after she eats and even seen her mom do it, she just has a fast metabolism. Trust me, she is just unique I have known her since we were 15, she is just amazing and even after I was a complete ass to her, even after I almost cost her a grade and even after I went to military school, she is giving me a chance and I don't intend to squander it. I don't know what I expect, but that is the beauty of it, I get to learn everything with her."

Logan felt a little jealous, he wanted that, truth be told he wanted Rory, "Well you are a lucky guy, I just hope she gives us a chance to help her in her new role as heiress. Do you think she knows?"

"She is clueless and Lorelai will just paint it with her broad hateful strokes, she really has a thing against wealth and privilege, yet she will exploit it. She ran from her duties, responsibilities and raised Rory with what is almost a phobia of Hartford, yet she put her in Chilton and wants her at Harvard. It is a strange message she sends her, it is almost like she wants her to be less than she can be and all she can be as long as she is broke." Tristan explained.

"That is so messed up!" Finn said and shushed the guys as the girls returned.

"Boys, did you bring your black cards? Are you ready to take Miss Gilmore here on her maiden shopping spree, we promise to let you carry all of our bags." Stephanie smiled devilishly and climbed into the SUV pulling Rory in behind her. Tristan was next and that left the boys to argue shotgun, Finn won. They drove to the mall and parked at Neiman Marcus, Stephanie looped her arms around Rory's arm, "They are going to hate and love this all at once, we are modeling all but the lingerie, we will be buying that too, but we only model that if they are very, very good."She snickered and Rory blushed.

"You aren't serious right, I mean, I can't model my underwear." Rory gulped and looked a bit panicked.

"No silly, that is for your guys eyes only, and only when you want, but we do get to tease them as we select items from the racks." Steph winked conspiritially.

"Steph, you may not buy lingerie on my card, keep that on Collin's, if I don't get to see it, I don't pay!" Finn protested then looked at Rory's rosey cheeks, "I will buy yours doll, if only to see that pretty blush."

Tristan smacked him, "She has my card and that will cover anything she wants or needs, capeesh?"

"Ooh, mob speak, he is serious about you girlie!" Steph giggled and led her first to shoes and purses.

They shopped for hours until the boys cried uncle and it was time for dinner, the breakfast had carried them all well past lunch the only person requiring anything was Rory with a steady intake of coffee.

"Luv, should you really drink that much coffee, it can't be good for you?" Finn had inquired.

"You would take my life's blood, the source of my soul the reason I live, you would deprive me of the one thing in this world that will always be true? Nay my good sir, you will not, for if you do you will suffer the wrath of my mother Lorelai the second and worse Lorelai the first will rain down hell's fire on you from England no less. Never speak of such blasphemy again and you are forgiven." Rory flicked her wrist at him disdainfully.

The group looked on in awe of her sudden regal behavior Finn dashed to a coffee stand and purchased her the largest cup available and dropped before her on his knees hoisting the cup above his head in penance.

"My good sweet Lorelai the third," He looked at her for confirmation and she nodded, "Take this cup from thy humble servant and forgive my error, I live only to serve."

The group was in awe of the display, it was as if they had played this game before she fit the group so well.

Rory took the cup and enjoyed a sip, "Your offering pleases us, you may rise and sin no more against the holy elixir."

Finn rose and bowed deeply raising her hand to place a kiss on her knuckles, by chance he glanced behind her and saw a t-shirt with a rhinestone coffee cup upon it and he made haste to the store purchasing three, hoping he guessed sizes correctly.

He presented the bag to her, "In further penance I offer bejeweled shirts for the three Lorelai's to enjoy in celebration of the gift that is coffee."

Rory looked at the offered gifts and burst into laughter, "So much better than a rhinestone penis." She continued laughing for minutes before she stopped and dried her eyes, noticing the confused looks she began "About a year ago my mom spilled coffee on her shirt well we were on our way to Friday night dinner and by happenstance she had had lunch with dad where he gave her a shirt with a rhinestone penis on it, she switched to the dry shirt and buttoned her jacket so only the tip showed, my grandmother insisted she unbutton the jacket and even after much argument my mother complied and you can only imagine the shock and horror my grandparents had at the brazen t-shirt, they will like this so much more, although I am sure my grandmother will never again demand my mother unbutton her jacket." Rory giggled again and Tristan pulled her to him so she could muffle her rapture in his chest.

"Christopher Hayden bought your mom a shirt with a penis on it, a rhinestone PENIS!" Colin was shaken, he found no humor in giving a penis shirt to the mother of your child.

"Cool your jets Collin, they were friends long before they had me, and heck they were only 16 when I was born, penis jokes, fart jokes, even queefs still send them into peels, they love South Park." Rory tried to explain.

"Do you ever wish they were together, like you know married?" Stephanie pryed.

"No, well maybe, and sometimes yes, it would make things easy, maybe I would have known you all sooner, lived more like you, but then would I be me? It is all so jumbled. Paris say's that in Hartford elite there is always a plan so I am stuck choosing between Tristan and Logan, what if I had chosen Finn or Colin? It is all so strange to me, I went to the Hayden's seeking family and what I got was a dynasty. My mom is angry, the Gilmore's are gleeful and the Hayden's they have plans. I had no idea that wanting to know them - my family, I was opening a huge can of worms. Dating Tristan has her panties in a wad, she gleefully bought a custom bumper sticker that says, "I left Hartford and all I got was CONFUSION!".

The group laughed completely understanding the joke. Rory leaned into Tristan and deeply inhaled his scent, it calmed and reassured her as nothing else ever had. This world, the one her mother had run from, it wasn't so bad, she had friends, access to funds and opportunity. She really couldn't understand what was so horrible her mother preferred to raise her in poverty than let her know this world. She knew her friends understood the need to flee, but she could not grasp it. The elite world, as she knew it, just made things easier, she tried to see the bad in it. She failed at seeing what was so very horrid about being accepted, wealthy and comfortable. Rory wondered if her comfort with these children of wealth and privilege was a betrayal of her mother, she was concerned her love of Tristan was akin to a slap in her mother's face. She worried that her mother would hate her, distance herself from her if she continued with her friendships. Then again she worried she would never be her true self if she stayed to the shadows of her mother's dreams. She was quite lost in all of her musings she had forgotten who she was with or where she even was.

"Hey, Mary, care to join us?" Tristan gently shook her shoulder."It looks like you are in a waking coma, are we boring you?"

"No. I am sorry, my mind is just a flurry of questions. I feel the need to make a pro/con list but have no idea where to begin, on the pro side is all of you and Tristan, obviously, but on the con I feel as if I am betraying my mom and that is HUGE, I mean I feel great with you all, but my mom feels that society is a trap, an evil, manipulating, controlling and money motivated trap. Realistically though, isn't everything? I mean, a job is just a way to control a worker, telling them how much they are worth, hell we are all selling out for something, some of us just have the comfort of money to sell out with." She ranted as she paced.

"You have a point there Ace", Logan said stilling her, "but the price is sometimes higher than we expect. The Dugrey's and Morgan's seem to have good marriages, my family and Steph's not so much. We are all Yale bound, no choice, all of us have spent years abroad living far from our families and sure we have limitless accounts at our disposal, that just means we will never have our parents attend a school play, a recital, any of it. Our parents only take interest when it may profit them and your friend Paris is not off when she tells you the Hayden's may have already chosen your destiny. You are probably Yale bound as well, that is where both of your grandfather's went. Truly that is probably why your mom chose to indoctrinate you on Harvard." He sighed and realized he was probably overstepping. "Do you agree Tristan?" He nudged the stilled girl towards him, he was the boyfriend after all, it was his job to be comfort and explain.

Stephanie noticed and sidled up to him placing her arm around his waist and he instinctively wrapped his arm over her shoulders. "Yeah girlie, you never know what the Hayden's might come up with. For now it's all tea and crumpets, soon they will start with the hints and then the gifts. You just never know what they will expect. You seem a nice respectable girl, that is a good thing, but it also means they will make demands all the more stringent."

They had finished loading the bags in the car and Tristan advanced they should try a local pizzeria and then head back to her town for the movie. The mood at dinner was lighter and several kids from school recognized the group and decided to follow them to the movie, this relieved Stephanie from being Logan's crutch, Missy would gladly fill that role and all the benefits she would not supply, there is only so much a girl can do for her best pals you know.

This would mark the beginning of many such adventures, slowly Hartford bleeding into the sleepy town. Taylor was over the moon for the increase in tourism and Lorelai seemed to accept that Rory was on the path she was meant to be. Lorelai didn't have to like this endeavor her daughter had innocently put into motion, but she did have to be there for her come what may.


	7. Chapter 7 - The Pied Piper

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

 **Chapter 7 – The Pied Piper**

Rory really enjoyed getting to know her grandparents and with the help of Stephanie's shopping skills and Tristan's generous black card she was beginning to look more the socialite and therefore was more readily accepted by her peers. Tristan loved the way guys patted him on the back for being with her, even the older men at the club looked at her with approval. She had always been well adjusted to the adult world but it was his job to get her to act her age more. It was to that end that he contrived to take her away for winter break, none of her new found friends would be in town, all jetting off to anywhere else and her only real obligation would be the Gilmore Christmas Gala and he could certainly have her back by then. His biggest obstacle would be her mother, he tried to find a place to take her that her mother may actually approve of. Then he remembered Stephanie talking about the Hayden's having a loft in New York, perhaps if he charmed them first … his mind was a whirl at the possibilities, he called the gang and began a plan.

Tristan sat in the imposing office of Judge Hayden awaiting the man himself. "Tristan, sorry to keep you waiting, to what do I owe the pleasure of a visit from the next generation?" The imposing man sat in his high-backed chair.

"Well Judge Hayden sir, as you know your granddaughter Rory and I have been dating for a while, winter break will mark six months. I understand you keep a loft in New York and as you know the Huntzberger's maintain a sizeable apartment. I want to know sir if I could request the use of your loft for the girls, the gentlemen will stay at the Huntzberger property and this way we will be able to show Rory the sights of Christmas in the city. It would only be for a week and we would return by the Gilmore Christmas Gala."

The steepled his fingers under his chin, "You pose an interesting proposition, you are eighteen and Rory is seventeen correct?" Tristan nodded, "I don't imagine Lorelai or Christopher have approved this outing." He stood and sat perched on the edge of his desk to appraise the boy. "You realize, that if you cause her to be any part of a scandal under your care, I will not treat it lightly. I know of your troubled past, it was I who recommended that particular academy." Tristan took in this bit of news.

"Sir, I have all of Hartford, a town called Stars Hollow and the Huntzberger heir waiting for me to mess this up, to that end only do I intend to disappoint." Tristan stared the man straight in the eye unblinking as he delivered his vow.

"The Huntzberger heir you say, he would make a fine match as well. I will take you at your word and the girls may use the loft, I suppose it will be Rory, Paris, Stephanie and possibly that girl from her town Lane is it?" I will add their names to the approved list as well as your own, be sure to be out as soon as you drop her off. I will have reports from the desk clerk, and he is a man I have known for years and trust." He gave Tristan a pointed glare and went around to his desk for the keys. "Don't think I have any sway with Lorelai, her word will be the final one, I am just approving your trip and providing safe lodging for my granddaughter."

"Thank you sir, I am sure to gain her approval in this. She may not approve of Hartford, but she does approve, at least a little, in the way I treat her daughter in it's regard." He took the keys and let himself out.

Straub sat back in his chair and considered the youth who had just left, the fool was already in love with the girl. He laughed and rose to share this bit of gossip with his wife and the Gilmore's. The boy bested the Hunbtzberger heir, he chuckled at the thought.

Tristan stood outside her office door, his plan was tight, he had a solid itinerary and a safe place for her daughter to stay, besides, she would be home for Christmas and then his parents soiree on New Year's she deserved this, her mom had to see it. He raised his fist to the door and rapped.

"Come in", Lorelai looked up and was surprised, "Tristan what are you doing here, is everything alright?" She waved at a chair inviting him to sit.

"I am coming to ask a huge favor and that you trust me. I have acquired the keys to the Hayden loft, the Huntzberger apartment and I am asking for five days and four nights before Christmas to show Rory Christmas in New York, she always has this far away look when she speaks of it as she had seen it in movies and I want to give that to her as a present. We will be reaching our six month anniversary and I think she will really love it. I even have a set schedule of events so you can see I won't do anything to jeopardize her stellar reputation." He handed her the folder he carried.

She flipped through it with interest, Radio City Music Hall, Rockefeller Center, Santa at Macy's, Tavern on the Green, a carriage through Central Park, it was sophisticated and playful, this boy really knew her daughter."So Straub gave you keys to the loft for her to use it, he must trust you. Did the old coot threaten you?"

"Of course, and he assured me your decision was law, he would do nothing to intervene." Tristan took note of her satisfied grin at this information.

"You have gone through a lot to make this happen? What do you hope to accomplish?" She steepled her fingers as Straub had. He wondered if she knew how alike they were.

"Rory has been through a lot, adjusting to new demands, new social status, it is daunting. I just want to give her a break, you know the requirements that will be made at both your parents and my parents parties, it is the only two we are forbidden from starting a sub party. It is going to be hell week when we get back, I just want her to have some fun before the other shoe drops." Tristan sat on the edge of his seat in hopes he had won.

"You really were born to be a lawyer kid. Okay, you have my blessing and once false step I tell Paris she can castraite you." She grinned in a way that he believed the threat.

"Got it, I will take good care of her and she will not be in one tabloid or see in any negative light on my watch." He rose to leave the room.

"Oh, and Tristan?" She began sweetly, "Remember you are eighteen, I have other recourse if you hurt her."

Tristan shook his head, "Are you sure you aren't Judge Hayden's girl, he said almost the exact same thing. I will tell you the same as I told him, I have too much at stake, too many people looking for me to fail to let them win. Have a good day Lorelai, I will go tell Mary the good news."

Lorelai laughed, she hadn't been compared to Straub for years, even her own father saw it. She shook her head, that boy was so in love with her daughter, at least he was one of the good ones.

Rory was so excited, she pulled the new red Tumi bag to the door and went to make coffee. Tristan had given it to her as an early Christmas present when he told her about the trip. Five whole days in New York at Christmas time, she couldn't wait to see all the window displays and people bundled up against the cold. She wondered if it was true that New Yorkers actually smiled at Christmas time. He had even convinced Mrs. Kim to let Lane come and he gave her a black Tumi. She bounced nervously on her sofa as she flipped channels and waited for the adventure to begin. She wondered what the loft would look like and if she could really get chestnuts. Her grandfather Gilmore had even given her her own black card, she assured him she would be judicious, he just smiled at her indulgently. Her grandmother had extracted promise that she use it to buy the dresses for the parties, shoes too if she liked. Rory was giddy, sure she could use Tristan's, but this was hers.

Lorelai entered the room a cup of Luke's to go for her daughter and an envelope of cash, $100, she knew it wasn't much, but she knew her daughter should have her own spending money. She looked at the Tumi bag, he did good, yes it was expensive, but not over the top and she knew from her patrons, it was built to last. It was nice he got one for Lane too, the boy really was considerate. She wondered how on earth he convinced Mrs. Kim to allow Lane in the fun.

"Well sweets, ready to abandon your poor mommy, the woman who slaved for you, kept a roof over your head and coffee in your cup for the Big Apple?" She teased.

Rory grabbed the cup from her mother, "Yes! Now I will see it all for myself, Paris might even let me do a lifestyles piece on it for the Franklin." Rory was giddy and Lorelai could not help but get caught in the current.

"Honey, I know grandpa gave you a black card, but here, it's not much, but it'll allow you to get a snowglobe at a bodega or something equally silly." She handed her the envelope and Rory hugged her tightly careful of the hot liquid in her hand,

"Thank you mom! This is so great of you! I know you were hesitant, but thank you so much!" Rory was enthusing as Lane came in the door.

"Chocolate, I need chocolate, my mom repacked my bag six times! I kid you not, I don't have anything in this bag that is not Mrs. Kim approved, I had to stop her putting the Jesus Saves sticker on it!" She quickly dragged the bag to Rory's room to raid her closet for age appropriate wear.

Rory went to the candy cupboard and retrieved a box of Godiva she had been saving for just such an occasion. They hastily repacked the bag and placed it by Rory's in the doorway. They then plopped onto the sofa to snack on the decadent treat. Lorelai had to admit the quality of junk food had certainly improved since Tristan started coming around.

Tristan walked in to the Crap Shack and quietly grabbed the bags to avoid the argument, then he returned for the girls, "So if you are done gorging are we ready to go?" He said in good humor.

Rory jumped up and ran to his arms, then kissed him sweetly, "We are so ready to go!"

Lane stood up to join her leaving the half eaten box on the table, "Yup, I have switched out my clothes and everything."

"Okay Tristan, she is my best friend and my baby, take good care of her and if anything happens to Lane leave the country, hell the planet, Mama Kim is a beast. Have fun kids!" She kissed the girls on the cheek and watched as they climbed into the waiting SUV.

The vehicle left and the teens pumped up the volume just out of city limits, the ride was ruckus and they wouldn't have it any other way.


	8. Chapter 8 - A Little Christmas

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

 **Chapter 8 – A Little Christmas**

They decided to first take the girls to the loft and get them settled. Rory approached the desk and provided her name and that of her guests, Tommy, the door man greeted her warmly, Miss Hayden, so glad you are here and I hope you enjoy your stay. Your grandfather left this for you as well. Welcome to New York and Merry Christmas!"

She entered the elevator and opened the envelope, it contained a note, a black card and a business card for the most exclusive dress shop in New York. The note read:

 _Dear Rory,_

 _We know we have only just begun to be a part of your life and for that we can never apologize_ _enough. Please accept this card, the dresses we have had made for you and the additions to the loft with all_ _of our love and sincerity. Enjoy this time with your friends._

 _Love your Hayden Grandparents_

Rory was touched she turned her tears into Tristan's chest, he pet her head and kissed the top, she took a breath. "Sorry guys, I was just a bit overwhelmed."

They arrived at the floor and the boys carried bags to the door, "OK Hayden, what adjustments do you think they made, brace yourself." Logan's tone was teasing and she appreciated the lightness he brought.

She opened the door and gasped, it was a Christmas paradise, there was a beautifully decorated tree with presents, a 2 ft tall gingerbread house with a working cookie train, the room was awash with twinkle lights and an abundance of read, green, silver and gold, in short it was beautiful. The group was in awe and the girls were all misty eyed, none of them had ever experienced such a lavish treat. The Hayden's were sending a message loud and clear, that they loved her, she was filled with delight.

Rory squealed, "Look everybody, its CHRISTMAS! They made me CHRISTMAS to make up for all they missed, I have to send them pictures, no, no a video, Tris I want you with me, Lane too and Paris, oh gosh I want you all, can we use a selfie stick is that tacky?"

They went around the lavish displays switching selfie stick from person to person gushing over the amazing things the Hayden's had provided. They ventured to the rooms and each one was personalized, Rory's knew hers by the book theme, Lane by the Hall of Music and Paris by the Teddy Bear Picnic, she couldn't believe they remembered, she loved teddy bears, only nanny ever seemed to remember, and there was a personal note for each girl on their bed, Stephanie didn't know the Hayden's well but was taken aback, her room had been outfitted in the theme of DaVinci's Venus Rising, she was touched beyond belief. They had seriously done the homework, each girl was beyond touched, spoiled and grateful. The boys were just a little jealous, knowing they would have no such treats, just a well appointed apartment.

Their first night in was a true cliché, Chinese and the movie 'Breakfast at Tiffany's' they toasted the week ahead and bid the boys adieu at night's end then the girls watched 'Girls Just Want to Have Fun' dancing, mocking and gorging on sweet treats.

The next day the boys arrived to take them skating, stopping at a famous deli where Rory declared 'I'll have what she's having' everyone laughed and Rory enjoyed her pastrami piled high with extra sauerkraut, extra pickle and double fries

They skated around Rockefeller Center then enjoyed hot cocoa's, roasted chestnuts and at Rory's insistence got hot dogs from a vendor cart, her treat. The girls returned to the loft to get ready for the concert they would enjoy at the Lincoln Center that night, they were giddy and all atwitter as they dressed.

"Rory, I thought you said you were on birth control?" Paris looked at her accusingly.

"What are you talking about Paris?" Rory looked at her incredulous and Lane and Stephanie stood with rapt attention.

"I went to your medicine cabinet to grab an aspirin and you don't have any pills." Paris had her arms crossed.

"Geesh Paris, not like it's any of your beeswax, I have an IUD, I was worried about hormones and it is safe, non-hormonal and I can never forget it." Rory looked at her with distain. "Seriously, what difference does it make Tristan and I aren't sleeping together."

At this revelation Stephanie gasped, "Really, still, you and he have been together forever and you still … wow Mary, that has to be a record for him, I haven't known him to go six days much less … WOW, just WOW!"

"Steph, calm down, he and I have talked, but I just … well honestly, protected or not, I am just not sure. I mean I care about Tristan, and I know he cares for me, but I just don't know if I am ready." She plopped on the couch and put her head in her hands.

Lane rubbed her back soothingly, "It's OK you know, to not be sure, even with all you guys have, there is no rush."

Paris perched on the table across from her, "Sorry for meddling, you are right, it's no one's business but yours."

"Yeah, I am sorry too girlie, I mean my first time I was so drunk I can't remember his name. You just wait until you are ready, it should have been more special, I just never was taught it was a big deal. In the circles we travel in most girls have been active as long as the guys, it's just another thing we do like drinking." Stephanie took the couch on the other side.

Rory took this new information to heart, "That's kind of sad, I can get why he is being so patient, I just don't know if I'll ever be ready. Honestly, between my mom and Mrs. Kim the whole intimacy thing sounds terrifying, then birth, eep, my mom said it's like doing the splits on a crate of dynamite. You can see why the whole thing scares me. I am just afraid it will be horrible, the whole thing will be horrible then I will have to do the splits on dynamite."

Stephanie realized she had only been ever told the down side, "It can be nice you know, I wouldn't do it if it wasn't nice, it can feel really great with the right guy. As for the dynamite, you are on birth control and I am sure Tristan will use a condom to be extra safe. You shouldn't be so afraid of something that can really be, well great. I get that I was freaked and drunk, but I was thirteen, I know, not smart, but I do remember he was nice and he smelled good."

"That's enough about sex, let's get back to the point of this trip, Christmas in New York!" Paris jumped up enthused and the girls returned to getting ready.

Rory considered what Steph had said, "Steph, thanks, you didn't have to share all of that, and it helps, so yeah thanks."

Stephanie hugged her, "Anytime, hey and if you want to talk about it to someone who won't try to scar you for life, I am here okay?"

The rest of the trip was special, beautiful, amazing and uneventful, Rory was thrilled by the displays, the lights, the shows and super delighted with the dresses and could not wait to show them off. The group had explained the expectations of the events and although it seemed intimidating, she knew with her friends she could get through it.


	9. Chapter 9 - The Other Shoe

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

 **Chapter 9 – The Other Shoe**

It was New Year's Day and Rory was sitting on her sofa in shock, truth be told she had been pretty much in shock since Christmas Day, she had been warned, she had been coached but nothing could compare to the reality. She was credited with reuniting the Hayden's and Gilmore family's and putting the union of their two business back on track, she would be called upon to run it when she was 25, until then she would serve internships with both grandfather's for one month every summer until she graduated Yale. She had sat in the office of the Gilmore home while her life was spelled out for her. Her journalism career was now a thing of the past, she could indulge herself with the newspaper at school and even freelance when she was not interning. She could only think, 'Mom was right' over and over since that day. She had successfully taken her mom's careful plan and thrown it all away. She would not attend Harvard or become the next Christiane Amanpour, nope, she had a bigger and better life plan. Nope no decisions needed to be made on her part ever again, her life was planned, heck they even approved her boyfriend as part of that plan. How could this happen? All she had wanted was to get to know the Hayden's hear a few stories about her dad as a boy, learn about her history. She was lost in her thoughts, totally spinning out of control and she didn't even notice Tristan had come in.

"Mar, are you okay, I have been here ten minutes and you haven't moved. Can I help? Do you want coffee?" He gently reached for her and carefully caressed her back.

"This is why, huh, this plan, all the manipulations, this is why you acted out. You did those things, were horrible to me, all to try to avoid this, and stupid me, I was out, off the radar and I had to ruin it." She leaned into his chest.

"Ah Mary, sweet Mary you don't have to go as crazy as I did, but that is part of why they let me take you to New York, they wanted you to be ready. We tried, but I don't think anyone is ever ready. You aren't an idiot, you couldn't possibly understand or know. Me I want to be an engineer or an architect, something with math. I get to be an attorney, corporate 'no defending criminals for you young man it is unseemly' my father is fond of saying." He leaned in and kissed her cheek, well it was supposed to be her cheek, before they knew it they were in a full blown make out session. Things were heating up pretty quickly when remote fell off the sofa startling them both.

"Oh God! I am so sorry, I can't believe I did that. I just attacked you, I wanted to just forget and you were here being so sweet and smelling nice. My mom could have come in, and did I say I am sorry?" Rory was adjusting and staring at her shoes.

"Mary, look at me." Tristan lifted her chin and turned her to face him, "You never have to apologize regardless of your motivation to kiss me or anything else."

"It's just I feel so lost, I want to not feel lost. I want to feel, found. Gah, maybe they are right, I am not suited to be a journalist if I can't even use words to describe what I am feeling and have to attack my boyfriend just to separate myself from the new plan that is eating my brain with a really sharp spoon." She stood and exited to the kitchen to busy herself, he followed her in.

"When does your mom get home?" Tristan was leaning on the counter as she prepared the pot of coffee with practiced ease. He looked at her and thought, she can make coffee, I doubt her grandmothers or my mother are capable of doing anything other than ordering it.

"She is working late tonight so 10 maybe 11, and that is no promise, she loves to just 'pop in really quick' to make sure I am OK and that I ate dinner, did my homework don't have you hiding naked in the closet." She smirked at him.

"Well, it is only three now, why don't I take you someplace to de-stress, we can go to Hartford catch a movie or call our friends and hit some shops, the arcade, bowling …" he stalled as she looked at him appalled.

"Bowling, really, can you see Logan, Stephanie, Paris or Colin, bowling sure Finn and Lane might find it fun, even with the shoe rental. Bowling that is just, I don't know so pedantic and I can't imagine …" he cut her rant off with a kiss.

"OK got it no bowling, how about you and me drive up to the lake and feed the ducks, that always makes you smile." He wrapped his arms around her middle.

"Aren't your parents off to Madrid today?' She said with a glint in her eye.

Tristan looked at her and got her meaning, "Rory, no, not like this, I want you that is never going to change, but I don't want you to remember it like this as an escape from the stress you are felling. I love you too much to let you go through that. I want us to talk, make sure you are ready. You are right it can be a great escape and stress reliever, but not your first time." He pulled her to him, stroking her hair. "It's going to be okay, I don't know how, but it will be okay."

"So lake? We will watch the ducks and pretend I didn't just step into my mom's life from before she was pregnant with me." She kissed his nose and sighed. "I finally get what she was talking about, it's horrible, but I don't want my mom's way out, think I can just disappear to Cuba or get lost in the jungles of Vietnam? I don't want to be a lawyer or business mogul, I want to travel and report on what I see, I want to be a voice for the people. Now I won't even have my own voice, I will just be a vapid socialite until I take over then hand the reigns over so I can get married have 2.5 kids and force one or both of them into the plan. This sucks." She buried her head in his shoulder and sighed.

"Ducks it is, then a movie and dinner, call your mom, let her know and we will get out of here." Tristan directed.

Tristan led her to his car and they drove to the lake to watch the ducks. After about an hour of silence he couldn't take it anymore, "Are you disappointed, mad, what is it?"

"You love me? You said you loved me and I didn't say it back, I am such a self absorbed inconsiderate b …" He cut her off with a kiss.

"You are none of that, you didn't have to say it back, I know you care, that's enough for now." He reassured her, stroking her hair and caressing her face.

"That's not it at all I DO LOVE YOU! It's why I want to lose myself in you, it's why I want you to make everything go away, just for a little while. You mean everything to me, you have been my rock and you are so sweet wanting everything to be perfect, but it's not, it never will be again." She tossed the last of the bird feed into the lake and walked with her arm around his waist and his over her shoulder back to the car.

"I'll take you to my place and give you a massage, is that a fair compromise?" He offered as he opened her door for her to slide in.

"Can I be naked?" She teased.

"You will be the death of me yet." He chucked and reached over to grab her hand.


	10. Chapter 10 - What About ?

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

A/N: A huge thank you to all who follow, favorite and review, this story has been very Rory centric and I appreciate you all staying with it.

 **Chapter 10 – What About... ?**

Lorelai came back to the house to check on Rory, she was worried she would make a rash choice, get drunk, break some rules, sleep with Tristan. She wondered if that was happening yet, had it started in New York, would Rory talk to her about it? She called to her daughter then remembered she had called to let her know she was spending the day with Tristan. Her mind was awash with possibilities, would her daughter try her way out? No, she has an IUD, not so easy to forget. She needed to talk to her, to know what was going on, to know how she was dealing. She knew it was a huge responsibility that had been thrown at her daughter. The poor kid to have all of her dreams stripped away before Christmas day was over, hell before the lunch was served. How could the Hayden's and Gilmore's think that taking everything away from her on Christmas day was a great surprise. That they thought she would be pleased, giddy with the possibility of becoming an indentured Hartford business woman, wife, mother and finally president of the DAR. Her beautiful, smart independent girl would be shackled to a plan, the plan she and Christopher escaped, but now it was all on Rory's small shoulders. She returned to work, she would worry about this later. Suddenly she heard Scarlett O'Hara 'I'll think of it tomorrow, after all tomorrow is another day.' She locked the house and decided to stop at Luke's for coffee first. Why is it, when my life is hard the first person I think of is Luke? Am I more dependent on him than I think, is my mom right, we are idiots. Man, I need coffee.

"Luke, 'knock me down and rise me up again', coffee me hard baby." Lorelai plopped onto the stool by the register.

Luke cleared his throat and tried not to picture himself en flagrante with her, he would gladly do as she asked, but he knew she never meant her suggestions. He poured her a cup of coffee and grunted.

Rory returned to an empty house, it was 11:30 and she found herself in need, really desperate need of girl talk. "Steph, want to sleep over?"

"Be there in a few, should I bring a Finn pack?" Steph was already grabbing her overnight bag.

"Better not, my mom will be home tonight, I just need a sympathetic ear and boy translator." Rory sighed, the night had been great but Tristan held firm to his resolve that she calm down before they consummated their relationship, then he was her plaything.

Stephanie arrived and noted the Jeep in the drive, Lorelai was home, talks would be a morning thing, good thing she left the Finn-kit behind.

"She walked into the house easily and found Rory and Lorelai watching 'Pirates of Penzance' and stilled her laugh.

"Hey girls, thanks for the crash pad, Colin is making me crazy! You guys are my heroes! Really I needed the escape." Her tone was excited. "Is the trundle out?" Stephanie wanted to make sure they could still talk.

She had a feeling Rory was stressed and wanted to assure her about Tristan's love of her. She had a suspicion she had tried to seduce him, as she had, she never wanted Rory to know he was her first, he was kind, and gentle, but she never loved him, yet somehow she felt she betrayed them both.

"Hey Lorelai, thought you were out tonight, mind if I crash, Colin is on my last nerve, and the maid won't hold his calls, so I need to hide out." Stephanie began; "I hope it's okay, I'm not interrupting any special mom daughter time, am I?"

"No, just watching the 'modern major general' sing about his lack of being an orphan while Angela Lansbury tries to pass herself off as a youthful maiden. This movie cracks me up, anyway I should get back to the Inn, I should be there, no night manager and all, I just wanted to check on our girl, she hasn't been herself since the big reveal. Maybe you can help, I am sure you have your own plan to contend with. The junk cupboard is full and there are seven flavors of ice cream to choose from, go nuts. Well kiddo, I see you are in capable hands. Goodnight ladies, see you at Luke's for breakfast." Lorelai left reluctantly, she knew Rory was hurting, but she did have to work and at least she wasn't alone.

Stephanie popped into Rory's room and returned wearing her pajamas, "So girlie, what's up? You have been practically catatonic since Christmas. I know they laid a lot on your shoulders, but it's the cross we bear right?"

"Tristan loves me so he won't sleep with me." Rory said with a deep sadness, "He says my first time should be memorable and not a fix for depression."

"Ah girlie, he's right you know, you should have a great first time, one that you can recall with fondness. You have to know he is only saying what he thinks is best, he is changed so much since military school, he is so much more mindful of others." Steph rubbed her back, "Should I have a Finn pack delivered?"

"Thanks, but no, mom will 'pop by just in case' at least two more times tonight. I think she was about to ask me about my sex life, which is really a lack there of, just before you showed up. Your timing is impeccable by the way, I couldn't stand to have this talk with her. I mean, I am losing every dream I ever had, why can't I just lose myself in him?" Rory sighed.

"That's why", Rory looked at her quizzically, "it's because you lost everything he wants to make this thing yours to keep. Rory you have waited for the perfect moment, that I am so in love with you moment, he wants you to have that. He really loves you, you are one of the lucky ones."

Rory let her friends words sink in, "I didn't think of that, I just thought if I was going to be one of you I might as well get it over with, you know embrace the stereo type. What difference does it make if I am a virgin? I see what you mean though, it does make a difference, it set me apart, it is why I have him. Thanks Stephanie, you really made me feel a bit better. So shall we get ice cream and watch 'Tommy'?"

"Sounds like a plan, sugar coma meet acid trip." Steph agreed.

"Steph, what's up with you and Colin? You said he is bugging you, what about?" Rory turned to look at her friend with interest.

"He wants to be my boyfriend, you know exclusive. He sees what you and Tristan have and he wants it for us, he has been after me for days to commit." She revealed as she handed Rory an ice cream pint and grabbed one for herself.

"Why is that a bad thing, don't' you like him, maybe even love him?" Rory popped the top off her ice cream and handed Steph a spoon.

Steph dug a spoonful out and let the treat melt in her mouth as they returned to the living room, "I don't know that I want to commit, we are only eighteen, next year we start Yale, I am afraid he will get drunk at a party sleep with someone else and I will be crushed. I already have enough stress, keeping a monogamist relationship with a player like Colin? I don't know if I can trust him, honestly I don't know if I can trust me. If we fail I lose a really good friend, heck I might lose more than him if we mess up really bad. I am really afraid I will lose out on all of you if it goes badly."

"Well what if I screw up and Tris and I break up, then say I start dating Logan, would you hate me?" Rory argued.

Rory sat sideways on the sofa while Tommy played pinball, "You would date Logan?" Stephanie looked at her wide eyed.

"Maybe, I don't know, he is different that Tris, I mean it's not like I am planning my next boyfriend, it is an example, you know I would never date Colin or Finn and Robert, really?" Rory explained.

"Okay, say I date Colin, we are exclusive and I drunk hookup with, to use your example, Logan, would you still be my friend?" Stephanie absently poked the container of ice cream and watched Ann Margret dance spastically in front of the round mirror.

"Steph, no relationship comes with a guarantee, I thought I would still be with Dean and what if Tristan had never returned from that military school. There is no way to say what will and won't work, but if you never try you will never know. Heck, do you think we would even be friends if I hadn't been with Tristan, I would just be the weird girl who sits with her walk-man in the cafeteria." Rory enthused.

"That's what I thought, I just really like him and I don't want to lose everything we already have." Steph lamented.

"You know when I said yes to Tristan, I was taking a big risk too, my mom hates all things Hartford and I had to go and fix things with the Hayden's, start dating Tristan, meet all of you guys, my whole life could have been different, if say I never fixed things with the Hayden's, got back with Dean and kept my life between Chilton and Stars Hollow completely separate. Do you think we would even have met without Tris?" Rory restated.

Stephanie shrugged and got up to put the ice cream in the freezer, she was done and it was getting soft. Rory followed her example and considered making coffee.

"Tired? Maybe we should go to bed it's late and we have both had tiring days." Rory suggested.

"Yeah, and I have to have a long chat with Colin tomorrow, we should resolve our situation before school starts again." Stephanie agreed.

The girls were lying in the dark and Rory began, " I'm scared Steph, I can really muck this up, then I lose everything and every one."

"Stephanie was surprised by this, "I promise, no matter what happens, I will always be there for you."

No more was said, nothing was needed and the girls both fell into fitful sleeps.


	11. Chapter 11 - Change the Way of Life

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

 **Chapter 11 – Change the Way of Life**

Lorelai, Stephanie and Rory were walking back from breakfast and they were surprised by a guy on a motor cycle blocking their path.

"That ladies is a 2000 Indian 80-horsepower, 5 Speed, Close Ratio Andrews Transmission, and I want to get one!" Lorelai explained.

"Hey ladies, want to go for a spin?" Christopher began, "It's probably safer than whatever my parents have cooked up for Rory's future."

Christopher got of the bike placed his helmet on the seat and Rory leapt up to hug him and Lorelai sighed. Stephanie noticed the obvious vibe between Rory's parents.

"Well, it looks like you all have some catching up to do, see you later Ror, Lorelai, thanks for breakfast." She skirted around the bike and got into her car, and headed back home.

"Hop on kid, I'll take you for a spin," he lifted a helmet from the back of his bake and paused, "That is if it's okay with your mom."

Rory gave her mom pleading puppy dog eyes, "Please mom, I'll hold on tight I promise."

Lorelai sighed, "Fine, be safe!"

Rory beamed and plopped the helmet on her head and scooted up behind her dad on the bike. They took off and Lorelai returned to her house trying to figure out what Christopher was up to.

Christopher took a path he knew lead to a dirt road that led to the bridge he stopped, Rory got off the bike and he followed suit they took off their helmet and walked towards the bridge. They sat in the middle feet dangling above the water. They just held the bridge and watched the water pass under their feet. Christopher picked up a twig and dropped it in the water, it spun and twirled away under the bridge and out of sight. He observed Rory and noticed she was oblivious.

"Hey kid, tell me what is going on in that head of yours, my parents and your Gilmore grandparents ambush you on Christmas of all days and turn your life upside down and inside out. Talk to me kid." He held her hand under his own as she grasped the bridge frame.

"I want to be a reporter, I can go to Yale and be a reporter, I don't want to do business or law, I want to write. I wonder if I had met Logan first would they have let me be a writer then, am I being punished for falling in love with a Dugrey?" She lamented light tears pooling in her eyes.

"So you are in love with a Dugrey huh? I did not know that, tell me about him." Christopher prodded.

"He is beautiful, smart, caring and he won't sleep with me because I am upset." She rambled then paused realizing what she had just said. "Sorry Dad, I am upset I didn't mean to overshare."

Christopher was astounded but took a breath and considered his words, "He must really love you kid. It takes real commitment to say no to a Gilmore girl, I oughta know. Look at it like this, he has been in the stressful, your life is over before it began place. He wants you to have some good memories, and I can't believe I am saying this but I think he is right, you need to be happy, relaxed. You should be sure you are ready for that step, depressed and stressed over what is happening to you, that will make things miserable, not memorable."

"Wow dad, I can't believe you said that either, but thank you, you helped me understand. Now can you help me get over this crazy life plan?" She lifted her head from the bridge frame and laid it on her dad's shoulder.

"That my dear is a question for the ages and who is Logan?" He watched as she bowed her head embarrassed.

"Apparently he is the only other logical choice, There is Tristan, he is bound to be a corporate lawyer and my current boyfriend, Logan is the Huntzberger heir, the only other logical choice for a girl of my breeding." Rory explained.

"I get it, you wonder if you had pinned your wagon to the newspaper family, would the grandparents have allowed you to have your dream. Let me assure you now, the answer is no, they would have conspired to ruin your relationship with Logan in favor of Tristan, that was always the plan kid. It was the plan that Lore and I marry, I take over after the merger when I was 25 and then Lorelai is the president of the DAR and we would have at least 3 kids and a dog by now. We just had other plans, you don't have to take our way, but you don't have to take the plan either. You and only you have control over your life, you want to write, write, this isn't the dark ages, you have free will. What is the worst thing that happens if you change the plan, you write, have a good life and hire someone else to manage the dynasty. I wish I had thought of that when I was a kid, but it's the truth, share it with your friends too, feel free, be free sweetheart, no one can control you without your permission, not even your grandparents." He kissed the top of her head and squeezed her had reassuringly.

"Really, I can still choose my own destiny, all my friends from Hartford seem to think they have no choice.

"That is because that is the lie they were sold, they have been taught from the cradle that they have a plan and a set destiny, truth is you make your own, everyone does. If their business fails, why should it be on you, businesses, change hands, fail and it happens, you are only ultimately responsible for you. It took me years to figure that out, get my parents out of my head, but I finally figured it out. You can choose your life kid, they can't. He wrapped his arm around her and let it all sink in.

"Dad, thank you, this talk has helped so much, first with Tristan and now with the plan. With you in my corner I know I can move forward and I know mom will stand by me, Tristan too, and we can help him become an architect and Steph a designer, I think Logan actually likes the news biz, so no help needed there. This helps dad, it really does. Now can we make Taylor crazy and circle the gazebo?" She smiled genuinely for the first time since Christmas she felt she could be happy again.

They took two turns around the gazebo and returned to her house parking behind the jeep, she was happy as she got off and she rushed towards the house, "Mom, I have choice, I have a choice! Dad explained, I have to call Tristan, I can't believe I didn't think about it, I have a CHOICE!" Rory screamed and twirled with her mother, then ran to make her call slamming her door behind her.

"Tristan come get me, we have to talk, it is super important, and I LOVE YOU!" She hung up before he could respond and pulled her favorite sweater over her head and took her book and went to wait for him on the patio.

She was lost in her book and didn't hear his car crunch in the driveway, he got out slammed the door of his car and smiled at the fact she didn't flinch, she was more herself right now and he couldn't wait to see what had caused this change. As he sat beside her Lorelai and a man he knew to be Christopher Hayden came out.

He rose leaving her to her reading, "Hello sir, I am Tristan Dugrey and I am dating your daughter."

Christopher thought about his conversation with her earlier, "I know, walk with me a moment, Rory will be okay I doubt she knows anything is happening outside of her book."

Tristan nodded and the men walked towards the gazebo, "Sir, is there a problem?"

"No, and please call me Chris, I had an interesting talk with my daughter today, she told me you wouldn't sleep with her because she was upset. Thank you for showing good sense, I am not happy about the prospect of her having sex before I die, but I am glad you are so respectful of her, it makes me feel she won't be treated badly. No father wants to think of his daughter in a grown up relationship but based on what she told me you are one of the good guys, and no father could ask for more for his little girl. Don't get me wrong, you hurt her and you will never recover from the hurt I extend to you, so just keep on respecting her and I think we will get along."

"Sir, I mean Chris, I can't tell you how odd hearing that Rory told you about that, it is very weird. I will assure you though I have no intention of disrespecting her ever. She is amazing and you should know I love her, I know what does an 18 year old know about love, I know Rory and she makes my day brighter and she gave me this chance, I have no intention to squander it." Tristan stood tall before the man.

Chris indicated they could return to the house, "That is good to know, thank you for confirming my suspicion about you, you are a good guy, and if you keep it up you will be a good man. I am telling you the same thing I told my daughter, you have a choice, be who you want to be, they can have their plans, but your future is on you, make of it what you will.' He patted Tristan on the shoulder as they approached the patio to a now alert Rory.

She jumped off the patio and into his arms, her knees lifted looking like a stilled image from a Lifetime movie promotion, "Tristan, you are here, I missed you!" She peppered him with kisses. They actually twirled and both Lorelai and Chris were taken by the scene.

"Can we go to the lake, I have so much to tell you? Did you meet my dad, he fixed, well everything, we are going to be okay, I can write. I love you and we can be happy!" She was delirious and he was relieved, sad Rory was difficult to deal with.

"Yeah, let me say bye to your parents and we can go feed the ducks."He approached Lorelai and Chris who looked at him conspiratorially.

"So is feeding the ducks some kind of code?" Lorelai teased she knew they went to feed the ducks for talks, but she loved to tease.

"Yes Lorelai, you caught us, it is code for us escaping to Vermont and having a clandestine marriage, then moving to Pigeon Ford, TN to become performers at Dollywood."

Christopher laughed, "He's got you there Lore, we can't stop them getting married in Vermont and once Dolly has them they are completely out of our reach, just hope Rory can do 'Jolene' justice."

"I figured her for more the 'I Will Always Love You' type." Lorelai responded and the three of them chortled. " Tell Stanley hello and don't let Kirsty Alley hog all the treats."

Tristan just shook his head and chortled, "Be back in a couple of hours, Chris Thank you, Rory is genuinely happy and knowing why gives me hope. Lorelai, he is a good one too, see you later."

"Okay, so now I have to know, what did you say, what happened?" Lorelai looked at him as if he invented fire.

Christopher shot her a smirk, "Just put it in her and his mind that the plans don't matter, they have choice, it's a free country and their success is their own."

"Ohh, smart boy, I knew I procreated with you for a reason. You do know that now Rory is happy they may actually sleep together? Can you handle that?" She looked at him expecting his appall.

"You know, after the talk Rory and I had today I am oddly okay, he loves her, he is kind and patient and he didn't take advantage when she insisted", he noted her puzzlement, 'she offered, he said no, not until they both agreed', he respects her, I have to admire that. Granted, we both want her to be a virgin 'til we die, it is going to happen sooner than that, and at least he cares enough to believe he loves her and she believes she loves him, it is more than many get."

"Wow, the force is strong with that one, he can resist the Gilmore Girl whiles, and pray tell sir how did you know this when I did not?" Lorelai was curious.

"I let her be free, and freedom is a great friend to truth." He replied.


	12. Chapter 12 -Epilogue

Story prompted by: roganjalex: Rory starts a relationship with Christopher's parents after the dinner at the Gilmore house

Disclaimer: No profits being made here, just flights of fancy, please don't sue.

 **Chapter 12 -** Epilogue

The photographer positioned the lovely bride in front of the mirror and adjusted the lights and himself so they were out of the frame, he knew the groom would enjoy seeing her reflecting on her life just before she married him. Rory stood gazing into the mirror, today was her wedding day, the sun was shining the birds were singing and all was right in the world. At 26 she could look back at her life happily, she had traveled as a reporter and found she hated it, after convincing her boss to let her go to Afghanistan, she had to resolve things and finally let him go, she called it quits, foxholes were not her forte, she liked clean laundry, a soft bed and darn it all she really missed him. That had been two years ago, he had supported her travels but he was so happy she was home. She reflected on there moment, that moment that changed everything, she had been shot, it was just a small leg wound, you wouldn't really notice unless you looked and knew where to look, but he had met up with her in the military hospital as soon as he was able, then he traveled with her through everything, physical therapy, quitting her job only to be offered a featured column, they really liked her and thought the newspaper industry would be poorer for the loss of her voice. She remembered standing by her mom on her big day eight years ago, she was misty over the thought that her twin siblings were the ring bearer and flower girl. Everyone had been surprised that Lorelai announced she was pregnant again, but that it was Christopher, Rory's father, that was even bigger surprise. Rory was excited that her parents would be married at last as were the Hayden's and Gilmore's. Chris even joined the firm making her freedom secure, then when mom had a boy, her plate was completely cleared of being the face of the two families. She recalled the boy she had dreamt would be waiting at the top of the aisle, she had lost him to his love of country and mortar fire he took saving a child's life they had been together for so long she never thought she would recover, then he the man waiting at the end of the aisle took her to a party in the woods and convinced her to jump, it was a reunion of the LDB, she was a member, but hadn't participated much in the reunion events, especially since her loss and he convinced her she needed to get back to the living it was what Tristan would have wanted. He later revealed he had loved her from afar for years and now that he had a chance he was going to stay the course. He was true to his word, she never had reason to doubt him, and today she would be tied to him in holy matrimony for the rest of her life.

"Ready for this sweetie?" Lorelai said as she walked in the door.

"You know mom, I really am. I feel like he is okay with this, he an Logan were so close. I miss him, but not as I used to, now he is like a sweet memory, is that bad?" Rory's eyes were misty.

"No honey, it's perfect, he never wanted anything but for you to be happy, protected and loved and you are, come on, your destiny awaits." Lorelai led Rory to her waiting father.

*End*

A/N: I know you were all hoping for a longer story, but I hope you are happy with the resolution. Keep an eye out though I am almost finished with another story and will be posting soon! Thanks for all of your support!


	13. AN for this story

Thank you for reading this story. I apologize if you were thrown by the ending. When I mapped this story, I always intended Rory to marry someone else. It was always to be her memory of her first love on her wedding day. In my mind a legacy is something from the past remembered, like an inheritance or the stories we tell children of their long past family members.

I hope you enjoyed it any way.

Your friend,

nightnovice


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